Nitrogen → 3-Piperidin-1-yl-pyrrolidin-2-one

HRID 1670824Notes

Reaction equation

HRID 1670824 reaction equation
C([O:3][C:4](=O)[CH:5]([N:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1)[CH2:6][C:7]#[N:8])C.N#N>CO>[N:9]1([CH:5]2[CH2:6][CH2:7][NH:8][C:4]2=[O:3])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

4

Reactant 2

HCID 947NitrogenHCID 673547353-Cyano-2-piperidin-1-yl-propionic acid ethyl ester

Product 1

HCID 576580133-Piperidin-1-yl-pyrrolidin-2-oneYield 59%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

Purge a mixture of 3-cyano-2-piperidin-1-yl-propionic acid ethyl ester (2.36 g, 11.2 mmol) and PtO2 hydrate (0.400 g) in methanol (40 mL) with N2 and stir under 50 psi of H2 at 50° C. for 16 hours. Cool the reaction and filter through hyflo. Remove the solvent from the filtrate in vacuo to afford crude product and purify with a 0 to 10% methanol in CH2Cl2 gradient to afford 1.11 g (59%) of the titled product. Rf=0.18 (9/1 CH2Cl2/methanol). ES MS (m/z): 169 (M+).

Workup

  1. customPurge
  2. temperatureCool
  3. customthe reaction
  4. filtrationfilter through hyflo
  5. customRemove the solvent from the filtrate in vacuo
  6. customto afford crude product
  7. custompurify with a 0 to 10% methanol in CH2Cl2 gradient

Sources & evidence

ORD record
ord-3163660fa874447cb73b2b80c66e26e0
Source dataset
uspto-grants-2011_08
Patent number
US07994176B2

Reaction notes

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